Patent GB-557842-A (GB)
Title: New disazo dyestuffs
IPC: C09B33/10
Filed: 1942-05-06
Abstract: 557,842. Dyes. KNIGHT, A. H., STEPHEN, W. E., and IMPERIAL CHEMICAL INDUSTRIES, Ltd. May 6, 1942, No. 6075. [Class 2 (iii)] Primary disazo dyes are obtained by coupling a 1:8-aminonaphtholsulphonic acid component Z (1 mol.), having the 2- and 7- positions free, in acid medium with a diazotized component A which is either a nitroamine of the benzene or naphthalene series (1 mol.) or an acidylaminoaniline (1 mol.), such diazo component being devoid of sulphone, sulphonamide or hydroxy groups, and in alkaline medium with a diazotized amine component A<SP>1</SP> (1 mol.) of the general formula X-CO-NY-R-NH 2 , wherein X represents a monochloro- or monobromo-alkyl (C 1  to C 3 ) radice, R represents a m- or p-phenylene residue which may be substituted, e.g. by methyl, methoxy or sulphonic groups, and Y represents hydrogen, alkyl (C 1  to C 6 ), cycloalkyl, aralkyl, alkoxyalkyl or aryl. The products are applicable for dyeing animal fibres, e.g. wool or silk, e.g. they dye wool from an acid bath various shades of blue and black, fast to severe washing, sulphur stoving, milling, potting, perspiration and light. Specified components Z are the 4- and 6-sulphonic acids and the 3:6- and 4:6-disulphonic acids of 1:8-aminonaphthol. Specified components A are 2-, 3- and 4- nitroanilines, 2-chloro- or bromo-4-nitroaniline, 5-nitro-2- anisidine, 4-nitro-2-toluidine, 5-nitro-1-aminonaphthalene, 4-nitroaniline-2-sulphonic acid, 3- and 4-acetylamino-anilines 4-N-ethyl-N- acetylamino-aniline, 4-N-cyclohexyl-N-acetylamino - aniline, 4 - N-ethyl - N - benzoylaminoaniline, 4-N-#-chloropropionylamino-aniline, 4- N-ethyl-N-chloroacetylamino-aniline, 4-amino- 2-N - ethyl-N- #- chloropropionylamino - toluene and 4-N-cyclohexyl-N-chloroacetylaminoaniline. Specified components A<SP>1</SP> are the 4-amino- 1-N-ethyl, isopropyl, n-butyl, sec-butyl, benzyl, cyclohexyl, and phenyl derivatives of chloroacetanilide, the 4-amino-N-ethyl and benzyl derivatives of 2-chloroacettoluidide, the 4- amino-N-ethyl derivatives of 2-α- and #-bromopropiontoluidides, 3-amino-chloroacetanilide-4- sulphonic acid, 2-amino-4-N-ethyl-chloroacettoluidide, 4-amino-2-N-ethyl-α-bromobutyryltoluidine, 4-amino-2-N-ethyl-#-chloropropiontoluidide, 4-amino-1-N-ethyl-#-chloro- or bromo-propionanilide, 4-amino-chloroacetanilide-3-sulphonic acid, the 4-amino-N-ethyl and benzyl derivatives of 2-chloroacetanisidide, 4- amino - 1 - N - n - butyl - chloroacetanilide-2-sulphonic acid, 4-amino-1-N-ethyl-bromoacetanilide, 5 - amino - 2 - N-cyclohexyl-chloroacettoluidide, 3-amino-1-N-benzyl-chloroacetanilide and its 2-sulphonic acid, the 4-amino-1-N- cyclohexyl derivatives of bromoacetanilide and α- and #-bromo- and #-chloro-propionanilides, 4 - amino - 1 - N-cyclohexyl-chloroacetanilide- 2- sulphonic acid and 4-amino-1-N-#-ethoxyethylchloroacetanilide. Examples relate to the production of the dyestuffs, (1) 4-nitroaniline or 2-chloro-4-nitroaniline # (acid) 1:8:3:6- aminonaphtholsulphonic acid (alkaline) # 4- amino-2-N-ethyl-chloroacettoluidide, (2) 4- nitroaniline # (acid) 1:8:3:6-acid (alkaline) # 4-amino-1-N-cyclohexyl-chloroacet- or #- chloropropion-anilide, (3) 4- nitroaniline # (acid) 1:8:3:6- acid (alkaline) # 4-amino-2-N- benzyl-chloroacettoluidide, (4) 4-acetylaminoaniline # (acid) 1:8:4-aminonaphtholsulphonic acid (alkaline) # 4-amino-1-N-ethyl-chloroacetanilide, (5) 4-nitroaniline # (acid) 1:8:4- acid (alkaline) # 4-amino-1-N-ethyl-chloroacetanilide or 4-amino-2-N-ethyl-chloroacettoluidide, (6) 4-nitroaniline # (acid) 1:8:4:6- aminonaphtholsulphonic acid (alkaline) # 4- amino-1-N-cyclohexyl-chloroacetanilide, (7) 3- nitroaniline # (acid) 1:8:3:6-acid (alkaline) # 4-amino-1-N-ethyl-#-chloropropionanilide, (8) 4- amino - 1 - N - cyclohexyl - chloroacetanilide # (acid) 1:8:3:6-acid (alkaline) # 4-amino-2-N- ethyl-#-chloropropiontoluidide. A table is also given showing the shades obtainable on wool with the dyestuffs from various combinations of components. Specifications 544,409 and 553,204 are referred to. 4-N-ethyl-N-acetylamino-aniline is obtained by acetylating 4-nitro-N-ethyl-aniline and reducing the nitro group.